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Preparation of levulinic acid esters from alpha-angelica lactone and alcohols

a technology of alpha-angelica lactone and levulinic acid, which is applied in the preparation of ester-hydroxy reactions, organic chemistry, fuels, etc., can solve the problems of limited commercial use of levulinic acid esters and low-cost route to manufacture of these esters

Inactive Publication Date: 2005-09-29
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commercial use of levulinic acid esters has been limited due to the high cost of production.
The production of levulinic acid esters from renewable resources, such as cellulosic biomass, however, represents a potentially low-cost route to the manufacture of these esters.

Method used

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  • Preparation of levulinic acid esters from alpha-angelica lactone and alcohols
  • Preparation of levulinic acid esters from alpha-angelica lactone and alcohols
  • Preparation of levulinic acid esters from alpha-angelica lactone and alcohols

Examples

Experimental program
Comparison scheme
Effect test

example 1

General Procedure for the Reaction of Alcohols and α-Angelica Lactone

[0057] A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, α-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard.

[0058] The examples described below were performed according to a similar procedure under the conditions indicated for each example.

examples 2-19

[0059]

Reaction of α-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) toProduce Butyl Levulinate (BuLV)N2AGLBuLVExpt.TimeTempPressureConversionSelectivityNo.Basic Catalyst(hrs)(° C.)(MPag)Feedstock(%)(%)2Et3N31005.52AGL (30%) / 1-77.5629.08BuOH (70%)3Et3N11505.52AGL (30%) / 1-89.0345.68BuOH (70%)4Et3N31505.52AGL (30%) / 1-98.8851.31BuOH (70%)5Dabco ™31505.52AGL (30%) / 1-99.2258.01BuOH (70%)620%31505.52AGL (30%) / 1-96.9755.68CsOAc / KA-160BuOH (70%)SiO2720%31505.52AGL (30%) / 1-98.9653.36RbOAc / KA-160BuOH (70%)SiO2820%11505.52AGL (30%) / 1-91.8737.56CsOAc / KA-160BuOH (70%)SiO2920%11505.52AGL (30%) / 1-95.4242.01RbOAc / KA-160BuOH (70%)SiO21020%31005.52AGL (30%) / 1-62.5920.94CsOAc / KA-160BuOH (70%)SiO21120%31005.52AGL (30%) / 1-63.2121.98RbOAc / KA-160BuOH (70%)SiO212Li2CO331005.52AGL (30%) / 1-22.5279.06BuOH (70%)13Na2CO331005.52AGL (30%) / 1-71.7332.81BuOH (70%)14K2CO331005.52AGL (30%) / 1-59.1762.23BuOH (70%)15Sc2CO331005.52AGL (30%) / 1-33.8164.46BuOH (70%)16Li2CO311505.52AGL (30%) / 1-62.9182.62BuOH (70%)17Na2CO311505...

examples 20-23

[0060]

Reaction of α-Angelica Lactone (AGL) with Cyclohexanol(CyHxOH) to Produce Cyclohexyl Levulinate (CyHxLV)N2AGLCyHxLVExpt.BasicTimeTempPressureConversionSelectivityNo.Catalyst(hrs)(° C.)(MPag)Feedstock(%)(%)20Li2CO311505.52AGL37.5638.03(30%) / CyHxOH(70%)21Na2CO311505.52AGL79.8114.82(30%) / CyHxOH(70%)22K2CO311505.52AGL94.072.32(30%) / CyHxOH(70%)23Cs2CO311505.52AGL80.6010.28(30%) / CyHxOH(70%)

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Abstract

The present invention relates to a process for producing levulinic acid esters from α-angelica lactone and alcohols in the presence of a basic catalyst. In addition, a method is described herein for producing fuel or fuel additives comprising levulinic acid esters produced from α-angelica lactone and alcohol. In addition, compositions are described comprising levulinic acid esters for use as fuel or fuel additives.

Description

FIELD OF THE INVENTION [0001] This invention relates to a process for producing levulinic acid esters from α-angelica lactone and alcohols in the presence of a basic catalyst. This invention also relates to the use of levulinic acid esters as fuel and fuel additives for gasoline fuel, diesel fuel and biofuel. BACKGROUND OF THE INVENTION [0002] Levulinic acid esters are useful as solvents, plasticizers, flavoring agents and chemical intermediates. Levulinic acid esters also exhibit characteristics that make them particularly suitable for use as oxygenate additives for diesel fuel, gasoline fuel and biofuel, octane number-enhancing agents for gasoline, and as cetane number-enhancing agents in diesel fuels. The commercial use of levulinic acid esters has been limited due to the high cost of production. The production of levulinic acid esters from renewable resources, such as cellulosic biomass, however, represents a potentially low-cost route to the manufacture of these esters. The pro...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C67/03C07C69/74C10L1/18C10L1/19C10L10/10C10L10/12
CPCC07C67/03C10L1/19C10L10/10C10L10/12C07C69/716
Inventor MANZER, LEO ERNEST
Owner EI DU PONT DE NEMOURS & CO
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